If you're looking for a place to enjoy a leisurely stroll, run, or bike ride in the Oakland hills, Shepherd Canyon is a nice park to check out. The park has a walking trail (known as the Montclair Railroad Trail) that is located just behind Montclair Village and is about 1.5 miles long (3 miles round trip). This trail is paved and almost completely flat, and it runs behind homes and through pretty tree groves. Aside from the paved trail, there's also a children's play area, large grassy field space, and a small scenic overlook. There are also several rest benches and some neat interpretive trail signs that detail the history of Shepherd Canyon. Apparently, this trail use to be an urban railroad and was also known as highway 77.
Along the trail, you'll find an adorable community garden and a neat little area up on the hill where skateboarders test out their tricks. There are also helpful mile markers throughout the trail. Part of the trail runs along Skyline blvd through the upper hills neighborhood. It's pretty easy to connect to other popular regional parks from the trail at Shepherd Canyon Park such as Sibley, Huckleberry, and Redwood Regional Parks. Since the trail is flat and easy, you'll find a lot of young children, families, and elderly frequenting this trail. Since it's not as popular as the regional parks nearby, the trail isn't crazy busy and is mainly frequented by locals. I enjoyed my brisk walk through this quaint little park and trail, and will definitely be visiting again once the weather starts to warm up again. read more